Jack Brickhouse

When the Cubs’ Ryan Dempster hosts his annual Casino Night fundraiser, he and his teammates come decked out in white tuxedos with black bow ties. When fellow Cub Randy Wells hosted his benefit concert with Texas Red Dirt singer Stoney LaRue at Joe’s Bar Friday, a teammate would be considered dressed up if he was wearing a collar. “I don’t want to make it stuffy,” said Wells, wearing his cap backward and sporting a Waco Fire Rescue T-shirt at his troops-focused Boot Bash. “That’s not me. I keep it low key. Dempster does the tuxedo one. That’s cool, but that’s more the demographic for that kind of event. This is what you would wear to a...